AU736431B2 - Process for the stabilisation of acylglycerols comprising high amounts of (w) polyunsaturated fatty acids by means of gamma-clyclodextrin - Google Patents
Process for the stabilisation of acylglycerols comprising high amounts of (w) polyunsaturated fatty acids by means of gamma-clyclodextrin Download PDFInfo
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- AU736431B2 AU736431B2 AU25177/00A AU2517700A AU736431B2 AU 736431 B2 AU736431 B2 AU 736431B2 AU 25177/00 A AU25177/00 A AU 25177/00A AU 2517700 A AU2517700 A AU 2517700A AU 736431 B2 AU736431 B2 AU 736431B2
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- polyunsaturated fatty
- acylglycerol
- fatty acids
- acylglycerols
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- 235000020777 polyunsaturated fatty acids Nutrition 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 22
- 230000006641 stabilisation Effects 0.000 title description 6
- 230000008569 process Effects 0.000 title description 5
- 229920000858 Cyclodextrin Polymers 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 15
- 235000015872 dietary supplement Nutrition 0.000 claims description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- -1 alkyl modified glycerol Chemical class 0.000 claims description 3
- 230000000536 complexating effect Effects 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000010525 oxidative degradation reaction Methods 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims description 2
- 235000009917 Crataegus X brevipes Nutrition 0.000 claims 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 1
- 235000009685 Crataegus X maligna Nutrition 0.000 claims 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 claims 1
- 235000009486 Crataegus bullatus Nutrition 0.000 claims 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 claims 1
- 235000009682 Crataegus limnophila Nutrition 0.000 claims 1
- 235000004423 Crataegus monogyna Nutrition 0.000 claims 1
- 240000000171 Crataegus monogyna Species 0.000 claims 1
- 235000002313 Crataegus paludosa Nutrition 0.000 claims 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 claims 1
- 229920004482 WACKER® Polymers 0.000 claims 1
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 29
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 20
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 20
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 20
- 230000006698 induction Effects 0.000 description 17
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 230000003647 oxidation Effects 0.000 description 15
- 238000007254 oxidation reaction Methods 0.000 description 15
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 14
- 229940090949 docosahexaenoic acid Drugs 0.000 description 13
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 238000011105 stabilization Methods 0.000 description 4
- FPRKGXIOSIUDSE-SYACGTDESA-N (2z,4z,6z,8z)-docosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C(O)=O FPRKGXIOSIUDSE-SYACGTDESA-N 0.000 description 3
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 3
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 3
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 235000004626 essential fatty acids Nutrition 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 230000006806 disease prevention Effects 0.000 description 2
- 235000021323 fish oil Nutrition 0.000 description 2
- 125000005639 glycero group Chemical group 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000006864 oxidative decomposition reaction Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 1
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000006701 autoxidation reaction Methods 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 229940097362 cyclodextrins Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000003374 diacylglycerol group Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000020978 long-chain polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 125000001531 monoacylglycerol group Chemical group 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000003203 triacylglycerol group Chemical group 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 238000009888 wet rendering Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
- A23L33/12—Fatty acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/30—Encapsulation of particles, e.g. foodstuff additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Emergency Medicine (AREA)
- Nutrition Science (AREA)
- Animal Behavior & Ethology (AREA)
- Mycology (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Wood Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Edible Oils And Fats (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
rIUUIU II 28/5/91 Regulation 3.2(2)
AUSTRALIA
Patents Act 1990
ORIGINAL
COMPLETE SPECIFICATION STANDARD PATENT a a a Application Number: Lodged: Invention Title: PROCESS FOR THE STABILIZATION OF ACYLGLYCEROLS COMPRISING HIGH AMOUNTS OFo-3 POLYUNSATURATED FATTY ACIDS BY MEANS OF
GAMMA-CYCLODEXTRIN
a a a a The following statement is a full description of this invention, including the best method of performing it known to us SWB9901 P Process for the stabilisation of acylglycerols comprising high amounts of 0-3 polyunsaturated fatty acids by means of gammacyclodextrin.
The invention relates to processes for the stabilization of acylglycerols comprising high amounts of w-3 polyunsaturated fatty acids by means of y-cyclodextrin, to the complexes thus prepared, and to their use.
Cyclodextrins are cyclic oligosaccharides which consist of 6, 7 or 8 a(1-4)-linked anhydroglucose units. The S- or ycyclodextrins, which are prepared by, for example, enzymatic starch conversion, differ in the diameter of their hydrophobic cavity and are generally suitable for the inclusion of a large 15 number of lipophilic substances.
Acylglycerols comprising high amounts of w-3 polyunsaturated fatty acids as for example eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), docosatetraenoic acid (DTA), or 20 docosapentaenoic acid (DPA) are employed in the food or dietary supplements sector to provide essential fatty acids, these essential fatty acids have been linked to the overall health and wellbeing of humans and to the treatment and prevention of diseases associated with the cardiovascular system, inflammatory disorders, human development, fitness and performance.
The main problem for the wider use of these substances is their limited stability. This results from their enhanced sensitivity to oxidative decomposition by exposure to light, atmospheric oxygen, heat or microorganisms) due to the large number of Carbon Carbon double bonds. Autoxidation takes place at.the C-C double bond, which primarily leads to the formation of peroxides and then to aldehydes, ketones and acids. Secondary reactions involve isomerizations and polymerizations.
WB9901 P 2 US 5,189,149 discloses a method of producing complexes of long chain polyunsaturated fatty acids, their salts and esters inclusive of fish and vegetable oil glycerides, with Pand y-cyclodextrin 0- and y-CD) and hydroxypropyl-pcyclodextrin, and the resulting complexes. This patent does not disclose the composition of their resulting complexes, or their stability.
The patents US 4,831,022, US 4,777,162 and US 4,775,749 disclose inclusion compounds of eicosapentaenoic acid and ycyclodextrin and food products containig the inclusion compound. These patents show that the complex has the highest eicosapentaenoic acid content when y-CD is used as i 1 cyclodextrin. The patents further disclose the high stability 15 of the eicosapentaenoic acid/y-cyclodextrin complex. The patents do not disclose complexes of derivatives of eicosapentaenoic acid or other e-3 polyunsaturated fatty acids with y-CD.
It is an object of the present invention to provide a method to stabilize acylglycerol comprising 0-3 polyunsaturated fatty acids against oxidative degradation.
This is achieved by a method in which y-cyclodextrin is mixed with acylglycerol comprising w-3 polyunsaturated fatty acids, either batchwise or continuously thus forming a y-CD/ acylglycerol complex.
The batches are mixed vigorously, i.e. kneaded or stirred vigorously, depending on the consistency.
The use of y-cyclodextrin allows better stabilization of the acylglycerols comprising w-3 polyunsaturated fatty acids than the use of c- or P- cyclodextrin.
Preparation from concentrated aqueous y-CD solutions has proved advantageous. The acylglycerols comprising w-3 polyunsaturated fatty acids are added to the aqueous y-CD WB9901 P 3 solution. The CD concentration of the aqueous solution before the addition of acylglycerol is preferably between 5 and 60 by weight. A CD concentration of 10 40 by weight is especially preferred.
The weight ratio of acylglycerols comprising w-3 polyunsaturated fatty acids to CD is preferably between 0.1 1 and 1, especially preferably between 0.4 1 and 3 1.
The mixing of acylglycerol and y-CD is preferably effected in a temperature range from above freezing point to 80°C. The process is especially preferably carried out at 10 60 0
C,
*particularly at approx. 15 50°C. The mixing time depends on S the temperature and is preferably between one hour and a few S 15 days. As a rule, a mixing time of 10 to 30 hours will suffice.
Complexing is preferably effected under atmospheric pressure.
Complexing is preferably effected under a protective gas atmosphere (nitrogen or argon).
S According to the present invention acylglycerol comprising w-3 polyunsaturated fatty acids preferably means mono-, di-, triacyl, or alkyl modified glycerol, glycerol mono-phosphate, comprising at least 1 o-3 polyunsaturated fatty acid.
o-3 polyunsaturated fatty acid preferably means a residue selected from the group EPA, DHA, DTA or DPA.
The especially prefered meaning of acylglycerol comprising 0-3 polyunsaturated fatty acid is mono-, di-, or tri-acylglycerol, or glycerol mono- phospate, with at least 1 EPA or DHA residue.
The most preferred meaning of acylglycerol comprising 0-3 polyunsaturated fatty acid is mono, di, tri-, acylglycerol comprising at least 1 EPA residue, in a preferred content of 30%, or at least 1 DHA residue, in a preferred content of WB9901 P 4 The composition of the w-3 polyunsaturated fatty acids of the acylglycerols can be determined in a known manner by gas chromatographic analysis of the corresponding methyl esters..
The acylglycerols comprising w-3 polyunsaturated fatty acids are obtained in a manner known per se, for example by wet rendering, often followed by continuous centrifugal separation of the fatty and aqueous phases. Open hydraulic presses, cage presses and continuous screw presses are all used in the final recovery of oil from the rendering residues, and the latter *are often solvent extracted after pressing.
Surprisingly, it emerged that acylglycerols comprising c-3 polyunsaturated fatty acids can be stabilized in an outstanding manner by complexation with y-cyclodextrin especially at EPA and/or DHA concentrations between 15% and (by weight) A markedly higher stabilization of the unsaturated compounds was found in comparison with a- and 0-cyclodextrin. When tested using a Rancimat machine the y-CD/acylglycerol complexes showed a much higher stability than those obtained with a- and P-CD.
The Gamma cyclodextrin complexes of acylglycerols comprising w-3 polyunsaturated fatty acids have a stability time on the Rancimat machine (Induction Time) in excess of 24 hours at 100 0
C.
The invention therefore also relates to a complex of y-CD and acylglycerols comprising e-3 polyunsaturated fatty acids.
A complex according to the invention consists of Gamma cyclodextrin comprising preferably 5 50 by weight of acylglycerols comprising w-3 polyunsaturated fatty acids.
WB9901 P Preferred is a content of 15 40 by weight of acylglyceroles comprising c-3 polyunsaturated fatty acids.
The acylglycerols comprising c-3 polyunsaturated fatty acids are preferably mono, di or triacylglyceroles comprising at least 1 EPA in a preferred content of 5 30%, or at least 1 DHA residue, in a preferred content of 5 The complexes, which are sparingly soluble in water, can be used directly in the form of the reaction mixture.
Alternatively, they can be isolated and processed by filtration, centrifugation, drying, grinding, sieving, screening, granulating or tableting to suit the procedure •which is customary in each case.
The complexes according to the present invention can be used, for example, in the food or dietary supplements sector to provide essential fatty acids. Numerous studies have linked w-3 polyunsaturated fatty acids with the treatment.and prevention of disease, especially of the Cardiovascular System, and Inflammatory Disorders, e.g. decreased risk of coronary heart disease, reduction in triglyceride levels, lower blood pressure, arthitis, asthma, Crohn's disease, psoriasis. In Human Development, especially for brain and retina growth and development, and improvements in Fitness and Performance, promoting aerobic endurance and mucle recovery.
The following examples are intended to illustrate the invention in greater detail.
In the examples the stability of the complexes made was measured by the Rancimat method. The 679 Rancimat machine is an instrument for the determination of oxidative and thermal stabilities. It is produced and supplied by Metrohm Ltd. (CH-9101 Herisau, Switzerland). In the case of oils and fats or substances containing oils and fats, the stability towards oxidative decomposition can be determined. The 679 Rancimat comprises a control unit and a wet section for 3 or 6 WB9901 P 6 rection and measuring vessels. In the wet section, the samples are exposed to a stream of atmospheric oxygen at elevated temperature. In the case of oils and fats, this gives rise to organic acids. The volatile decomposition products are trapped in a measuring vessel filled with distilled water and continuously detected with a conductivity cell. The control unit assumes control and evaluation of the measurements running in the wet section.
The oxidative resistance of the acylglycerol CD complexes was measured at 100 0 C. Evaluation was done using modes 1 (induction time) and 2 (stability time with AK set at pS/cm). In general, evaluation mode 1 (induction time) was used. Airflow of 20 L/h was used for all samples. Sample quantities of 2.0 g (solid complex) and 3.5 g (liquid fish oil) were used.
Induction Time is calculated from the curve K It is the time needed to reach the break point of the curve. The 20 induction time is a characteristic of the oxidative stability *.of the sample under evaluation and is in almost complete agreement with the results of the time consuming AOM method.
(Determination of the Oxidative Stability of Fats and Oils: Comparison between the Active Oxygen Method (AOCS Cd 12-57) and the Rancimat Method, JAOCS 792 795 (1986), L&ubli, M.W. and Bruttel, P.A.) Stability Time is calculated from the curve K It is the time needed to reach a preset conductivity change (AK set at 30 pS/cm).
Example 1: To 150 ml of deionized and degassed water at 600 C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the solids had dissolved, 22.0 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added. The mixture was stirred under a nitrogen atmosphere at 600 C for WB9901 P 7 24 hours then allowed to cool to ambient temperature. The resulting paste was dried under vacuum at 50 0 C for 48 hours.
The product was obtained as a white powder in a yield of 116.0 g Acylglycerol content: 18% by weight. Oxidation Induction time at 100 0 C (IT 1 0 >24 hours. Stability time at 100° C: >24 hours.
Example 2: To 150 ml of deionized and degassed water at 200 C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light then 22.0 g of acylglycerol solution containing approx. 5% EPA and min.
25% DHA was added and the mixture stirred under a nitrogen atmosphere at 200 C for 24 hours. The solid was removed and 15 dried under vacuum at 50 0 C for 48 hours. The product was obtained as a white powder in a yield of 118.3 g Acylglycerol content: 18% by weight. Oxidation Induction time at 100 0 C (IT, 0 >24 hours. Stability time at 100° C: >24 hours.
Example 3: To 230 ml of deionized and degassed water at 400 C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the solids had dissolved, 43.0 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added. The mixture was stirred under a nitrogen atmosphere at 40° C for 24 hours then allowed to cool to ambient temperature. The resulting paste was filtered to remove water then dried under vacuum at 40°C for 48 hours. The product was obtained as a white powder in a yield of 138.2 g Acylglycerol content: 30% by weight. Oxidation Induction time at 100 0
C
(IT
100 >23 hours. Stability time at 100' C: >20 hours.
Example 4: To 230 ml of deionized and degassed water at 400 C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the WB9901 P 8 solids had dissolved, 67.0 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added. The mixture was stirred under a nitrogen atmosphere at 400 C for 24 hours then allowed to cool to ambient temperature. The resulting paste was filtered to remove water then dried under vacuum at 50 0 C for 48 hours. The product was obtained as a white powder in a yield of 162.2 g Acylglycerol content: 40% by weight. Oxidation Induction time at 100 0
C
(IT,
1 >9 hours. Stability time at 100° C: >9 hours.
Example To 450 ml of deionized and degassed water at 400 C in a Stephan Mixer was added 200.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the solids had dissolved, 67.0 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added. The mixture was stirred under a nitrogen atmosphere at 40° C for 24 hours then allowed to cool to ambient temperature. The resulting paste was dried under vacuum at 50 0 C for 48 hours.
S 20 The product was obtained as a white powder in a yield of 250.4 g Acylglycerol content: 25% by weight. Oxidation Induction time at 100 0 C (ITo 0 >24 hours. Stability time at 1000 C: >11 hours.
Example 6: To 230 ml of deionized and degassed water at 40° C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the solids had dissolved, 25.0 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added. The mixture was stirred under a nitrogen atmosphere at 400 C for 24 hours then allowed to cool to ambient temperature. The resulting paste was filtered to remove water then dried under vacuum at 50 0 C for 3 days. The product was obtained as a white powder in a yield of 121.3 g Acylglycerol content: 20% by weight. Oxidation Induction time at 100 0
C
(IT,
0 >24 hours. Stability time at 1000 C: >24 hours.
WB9901 P 9 Example 7: To 230 ml of deionized and degassed water at 400 C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the solids had dissolved, 17.7 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added. The mixture was stirred under a nitrogen atmosphere at 400 C for 24 hours then allowed to cool to ambient temperature. The resulting paste was filtered to remove water then dried under vacuum at 50 0 C for 48 hours. The product was obtained as a white powder in a yield of 109.0 g Acylglycerol *content: 15% by weight. Oxidation Induction time at 100 0
C
(IT
1 0 24 hours. Stability time at 1000 C: >24 hours.
S 15 Example 8: (Comparison example) "To 50 ml of deionized and degassed water at 400 C was added 20.0 g of dry Beta-CD. The flask was covered to exclude light then 4.4 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added to the slurry. The mixture was S20 stirred under a nitrogen atmosphere at 40° C for 4 hours then allowed to cool overnight to ambient temperature. The solid was collected by filtration and dried under vacuum at 40' C to give 24.0 g of material as a light yellow powder.
Acylglycerol content: 18% by weight. Oxidation Induction time at 100 0 C (IT 00 3.1 hours. Stability time at 1000 C: 4.4 hours.
Example 9: (Comparison example) To 50 ml of deionized and degassed water at 400 C was added 20.0 g of dry Alpha-CD. The flask was covered to exclude light then 4.4 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added to the slurry. The mixture was stirred under a nitrogen atmosphere at 40° C for 4 hours then allowed to cool overnight to ambient temperature. The solid was collected by filtration and dried under vacuum at 400 C to give 11.7 g of material as a light yellow powder.
Acylglycerol content: 18% by weight. Oxidation Induction time at 100 0 C 3.4 hours. Stability time at 1000 C: 4 hours.
WB9901 P Example 10: (Comparison example) To 230 ml of deionized and degassed water at 400 C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the solids had dissolved, 100.0 g of acylglycerol solution containing approx. 5% EPA and min. 25% DHA was added. The mixture was stirred under a nitrogen atmosphere at 40° C for 24 hours then allowed to cool to ambient temperature. The resulting paste was filtered to remove water then dried under vacuum at 50 0 C for 48 hours. The product was obtained as a yellow-white powder in a yield of 195.07 g Acylglycerol Scontent: 50% by weight. Oxidation Induction time at 100 0
C
(IT
0 o) 6.7 hours. Stability time at 1000 C: 6.8 hours.
Example 11: To 250 ml of deionized and degassed water at 450 C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the solids had dissolved, 24.0 g of acylglycerol solution containing approx. 25% DHA was added. The mixture was stirred under a nitrogen atmosphere at 45" C for 24 hours then allowed to cool to ambient temperature. The resulting paste was filtered to remove water then dried under vacuum at 500C for 48 hours. The product was obtained as a white powder in a yield of 123.07 g Acylglycerol content: 20% by weight.
Oxidation Induction time at 100 0 C (ITo 0 >24 hours.
Example 12: To 250 ml of deionized and degassed water at 450 C in a 1-L reaction kettle was added 100.0 g of dry Gamma-cyclodextrin.
The reaction vessel was shielded to exclude light and once the solids had dissolved, 24.0 g of acylglycerol solution containing approx. 25% EPA was added. The mixture was stirred under a nitrogen atmosphere at 450 C for 24 hours then allowed to cool to ambient temperature. The resulting paste was filtered to remove water then dried under vacuum at 50°C for 48 hours. The product was obtained as a white powder in a WB9901 P 11 yield of 123.57 g Acylglycerol content: 20% by weight.
Oxidation Induction time at 100 0 C (IT 00 >24hours.
Results: In general, complexes of acylglycerol (25 by weight) with gamma-CD showed no oxidation over 24 hours while control samples of 18% acylglycerol mixed with alpha or beta CD showed rapid oxidation (less than 5 hours). Complexes of acylglycerol in excess of 40% however began to exhibit oxidation.
Chart of Results io:: Ex. No. Acyl- CD conc. Rxn. Temp. Rxn. Time Yield Induct. Time Stability glycerol (wt (hr) 100 0 C (hr) Time (hr) 1 18 40 60 24 95 >24 24 2 18 40 20 24 97 >24 >24 S 3 30 30 40 24 97 >23 4 40 30 40 24 97 9.2 00 5 25 30 40 24 94 >24 >11 6 20 30 40 24 97 >24 >24 7 15 30 40 24 93 >24 >24 o: 8 18 28 40 24 99 3.1 4.4 S 9 18 28 40 24 48 3.4 4 50 30 40 24 97 6.7 6.8 11 20 30 45 24 99 >24 n.d.
12 20 30 45 24 99 >24 n.d.
Acyl- 100 5 4 glycero 1 Acyl- 20 3.3 4 glycero 1 7-
CD
Mixture n.d. not determined lla "Comprises/comprising" when used in this specification is taken to specify the presence of stated features, integers, steps or components but does not preclude the presence or addition of one or more other features, integers, steps, components or groups thereof.
S* oo
Claims (9)
1. A method to stabilize acylglycerols comprising o-3 polyunsaturated fatty acids against oxidative degradation characterised in that y-cyclodextrin is mixed either batchwise or continuously with the acylglycerol comprising 0-3 polyunsaturated fatty acids, thus forming a y- CD/acylglycerol complex.
2. A method according to claim 1 characterised in that the acylglycerols comprising 0-3 polyunsaturated fatty acids are .added to an aqueous y-CD solution. *oo.
3. A method according to claim 2 characterised in that the CD concentration of the aqueous solution before the addition of acylglycerol is between 5 and 60% by weight.
4. A method according to any one of claims 1 to 3 characterised in a weight ratio of acylglycerols comprising -3 polyunsaturated fatty acids to CD between 0.1 1 and A method according to any one of claims 1 to 4 characterised in that the mixing of acylglycerol and y-CD is effected in a temperature range from above freezing point to 0 C.
6. A method according to any one of claims 1 to characterised in that the complexing is effected under a protective gas atmosphere (nitrogen or argon). IAN \fn^
7. A method according to any one of claims 1 to 6 characterised in that acylglycerol comprising 0-3 polyunsaturated fatty acids means mono-, di-, tri- acyl, or alkyl modified glycerol or glycerol mono-phosphate, with at least 1 0-3 polyunsaturated fatty acid.
8. A method according to any one of claims 1 to 7 characterised in that 0-3 polyunsaturated fatty acid means a residue selected from the group EPA, DHA, DTA or DPA.
9. A complex of y-CD and acylglycerols comprising a content of 15% 40% by weight of acylglycerols comprising -3 polyunsaturated fatty acids.
10. Use of a complex according to claim 9 in the food or dietary supplements sector. DATED this 17 t h day of May 2001 WACKER BIOCHEM CORPORATION WATERMARK PATENT AND TRADE MARK ATTORNEYS 290 BURWOOD ROAD HAWTHORN VICTORIA 3122 AUSTRALIA IAS:JPF:VRH P17151AU00
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP99106106 | 1999-04-01 | ||
| EP99106106A EP1041136B1 (en) | 1999-04-01 | 1999-04-01 | Process for the stabilisation of acylglycerols comprising high amounts of w-3 polyunsaturated fatty acids by means of gamma-cyclodextrin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2517700A AU2517700A (en) | 2000-11-09 |
| AU736431B2 true AU736431B2 (en) | 2001-07-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU25177/00A Ceased AU736431B2 (en) | 1999-04-01 | 2000-03-31 | Process for the stabilisation of acylglycerols comprising high amounts of (w) polyunsaturated fatty acids by means of gamma-clyclodextrin |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6878696B2 (en) |
| EP (1) | EP1041136B1 (en) |
| JP (1) | JP3935307B2 (en) |
| KR (1) | KR100370856B1 (en) |
| AU (1) | AU736431B2 (en) |
| CA (1) | CA2298346C (en) |
| DE (1) | DE69900155T2 (en) |
| DK (1) | DK1041136T3 (en) |
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| JP4116844B2 (en) | 2001-09-13 | 2008-07-09 | 花王株式会社 | Oil composition |
| DE10253042A1 (en) * | 2002-11-14 | 2004-06-03 | Wacker-Chemie Gmbh | Cosmetic preparation containing a complex of cyclodextrin and vitamin F. |
| BRPI0611925A2 (en) * | 2005-06-13 | 2010-10-13 | Cargill Inc | cyclodextrin inclusion complexes and methods for preparing them |
| KR20080023684A (en) * | 2005-06-13 | 2008-03-14 | 카아길, 인코포레이팃드 | Cyclodextrin inclusion complex and preparation method thereof |
| JP2009526033A (en) * | 2006-02-07 | 2009-07-16 | オメガトリ エーエス | Omega 3 |
| EP2027136A4 (en) * | 2006-06-13 | 2011-08-03 | Cargill Inc | Large-particle cyclodextrin inclusion complexes and methods of preparing same |
| EP2049083A2 (en) * | 2006-12-27 | 2009-04-22 | Cargill, Incorporated | Stabilisation by preparing cyclodextrin inclusion complexes |
| WO2008092115A1 (en) * | 2007-01-26 | 2008-07-31 | The Regents Of The University Of California | Conversion of glycerol from biodiesel production to allyl alcohol |
| US20080283693A1 (en) * | 2007-05-15 | 2008-11-20 | Evans Michael J F | Propulsion apparatus and system |
| JP2015062398A (en) * | 2013-09-26 | 2015-04-09 | サンデン商事株式会社 | Antioxidation-treated krill oil-containing supplement |
| JP2015159801A (en) * | 2014-02-28 | 2015-09-07 | サンデン商事株式会社 | SUPPLEMENT CONTAINING KRILL OIL ANTI-OXIDIZED BY γ-TOCOTRIENOL |
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| JPS6034156A (en) * | 1983-08-08 | 1985-02-21 | Hayashibara Biochem Lab Inc | Eicosapentaenoic acid clathrate compound and food and drink containing the same |
| JPS61233625A (en) * | 1985-04-08 | 1986-10-17 | Sanraku Inc | Oil and fat composition containing gamma-linoleic acid |
| IT1243192B (en) * | 1990-08-09 | 1994-05-24 | Staroil Ltd | LONG CHAIN POLYUNSATURATED FATTY ACIDS AND THEIR DERIVATIVES, WITH CYCLODESTRINE |
| DE19612658A1 (en) * | 1996-03-29 | 1997-10-02 | Wacker Chemie Gmbh | Process for the stabilization and dispersion of vegetable oils containing polyunsaturated fatty acid residues by means of gamma-cyclodextrin and complexes thus prepared and their use |
| PL191399B1 (en) * | 1996-10-28 | 2006-05-31 | Gen Mills Inc | Method of obtaining distinct particles of controllable release by embedding in a base and encapsulating sensitive components |
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1999
- 1999-04-01 DK DK99106106T patent/DK1041136T3/en active
- 1999-04-01 EP EP99106106A patent/EP1041136B1/en not_active Expired - Lifetime
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| KR20010006938A (en) | 2001-01-26 |
| US20030087879A1 (en) | 2003-05-08 |
| DE69900155T2 (en) | 2001-10-11 |
| CA2298346A1 (en) | 2000-10-01 |
| EP1041136A1 (en) | 2000-10-04 |
| EP1041136B1 (en) | 2001-06-13 |
| JP3935307B2 (en) | 2007-06-20 |
| DK1041136T3 (en) | 2001-09-17 |
| DE69900155D1 (en) | 2001-07-19 |
| AU2517700A (en) | 2000-11-09 |
| CA2298346C (en) | 2005-11-08 |
| KR100370856B1 (en) | 2003-02-05 |
| US6878696B2 (en) | 2005-04-12 |
| JP2000313897A (en) | 2000-11-14 |
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